The 9 Most Humiliating Losing Streaks in Sports

Cleveland may not be the most tortured sports city, but they sure do get a lot of press for it: Major League, the Browns, and of course, the Cavs sans-LeBron. Last night’s loss marked the Cavs’ 26th straight loss, tying the Tampa Bay Buccaneers for most consecutive losses by a professional team in North America. But when it comes to humiliating losing streaks, they are not alone.

The killer in these records is the duration. Losing 26 games in a row? That sucks. But losing 18 losing seasons in a row is a long, slow death. So run through these 9 record holders and wonder why they even bothered to keep showing up.

9. Anthony Young – 27 Consecutive Losses as a MLB PitcherFrom May ‘92 to July ‘93, Anthony Young didn’t win a game as a pitcher. That’s pretty crazy, but not nearly as crazy as the fact that he was picked up by another team during the slump. His journey to loserdom started with the Reds, and despite his mounting losses, he was taken on by the Mets, where is bad luck continued. Fans sent him good luck charms to turn the streak around, but can you even consider them good luck charms when they took so long to work?

8. The Caltech Beavers – 207 Consecutive LossesThe Caltech Beavers men’s basketball team (NCAA Div. III) hold the longest losing streak in NCAA history. Spanning 207 games and 11 years, the team went from 1996 to 2007 without a win. Their in-conference losing streak has lasted even longer. After last night’s loss to Pomona-Pitzer, the team has lost 307 consecutive conference match ups since 1985. It’s worth noting that the school has a strict admissions policy, which explains the lack of talented athletes. That said, why even have a team?

7. Tampa Bay Buccaneers – 14 Consecutive Losing Seasons (NFL)While the bucks are close to losing their record for consecutive losses, they can take comfort in the fact that they still hold another infamous record: 14 consecutive losing seasons. And while Detroit might give them a run for their money, I’m pretty sure it will belong to Tampa Bay for a while.

6. Washington Capitals and San Jose Sharks – 17 Consecutive Losses (NHL)Not AS humiliating as streaks in other sports, but dropping 17 games is still a bad six-week stretch. Washington had that run in 74-75 and San Jose in 92-93. San Jose was an expansion team in that era, so it’s a bit more tolerable, but the Capitals had no excuse. I could see this record coming down in the next few years. Simple math says this one isn’t strong enough to stand at 17.

5. Buffalo Bills – 4 Consecutive Super Bowl LossesWhat a weird record. You’re good enough to get into the Super Bowl four years in a row, but you’re bad enough to lose all 4 of those matches. How are you supposed to feel? Despite the frustration, I’d be pretty damn excited. Sure, you didn’t win the championship but (and I know this will read as “loser talk”) you get to enjoy the excitement of going to the Super Bowl four years in a row. When your team makes it to the big game, those two weeks before the Super Bowl are heaven. It’s a bad record, but not the worst.

4. Kansas City Chiefs – 7 Consecutive NFL Playoff LossesYou drop 7 in a row in basketball, baseball, or hockey and that’s just a couple seasons of torment. I mean, at least you got to the playoffs, right? Well, in football, 7 consecutive playoff losses means a generation of heartbreak. The kind of heartbreak 7-9 teams never feel. January 16, 1994 was their last win in the playoffs. 17 years without a modicum of validation for their efforts. The fact that KC has some of the best fans must make the situation even more bitter.

3. Cubs – 103 Year Championship Drought103 years. Could you imagine going your whole lifetime and never seeing your team win? Well, you could have lived 1.5 lifetimes and still never seen the Cubs celebrate. The Cavs are going through a humiliating streak right now, but this should be agony. The Cubs haven’t even shown up to the World Series since a few weeks after World War II ended. I understand that Cubs fans are happy-go-lucky, but this is ridiculous.

2. Cleveland Browns and Detroit Lions – No Super Bowl Appearances…EverThis isn’t exactly a losing streak, but it sure is humiliating. These two teams also share this distinction with Houston and Jacksonville, but the latter are fairly new teams, so I’ll leave them out of this. But Cleveland and Detroit? CLEVELAND AND DETROIT? That’s not like Tampa and Seattle. These are hubs of football that haven’t found themselves in a championship in the modern era. Recently, the Super Bowl has probably been the furthest thing from their minds as they fight to stay out of last place. It’s gotta kill both these football towns to be on the sidelines year after year.

1. Pittsburgh Pirates – Most Consecutive Losing MLB Seasons (18)The baseball playoffs are still probably the hardest to make, just based on numbers. Even so imagine not being able to muster a winning season for 18 years. And from the looks of it, it’s probably not going to end any time soon. Luckily, Pittsburgh has the Steelers to fall back on.